


Sin City

by italiandancer1275



Series: Supernatural [4]
Category: Supernatural
Genre: Baby, Elizabethville, F/M, Hunters & Hunting, Impala, Ohio, POV Female Character, Reader-Insert, Sioux Falls, South Dakota, Supernatural Elements, The Colt (Supernatural)
Language: English
Status: Completed
Published: 2018-02-06
Updated: 2018-04-04
Packaged: 2019-03-14 16:55:25
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 9
Words: 9,204
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13594374
Author URL: https://archiveofourown.org/users/italiandancer1275/pseuds/italiandancer1275
Summary: See what happens when the three of you investigate some "boarded-up factory town" that has turned to sex, drugs, and sin!Y/N= Your nameY/N/N= Your nickname





	1. Case #3

It had been about a week since you’d learned of Sam’s powers (still extremely weird to say…or think or whatever). To say it was an awkward week would be an understatement. Sam was on edge, as you still hadn’t given him concrete support on whether or not you thought he was a freak. To be fair, you didn’t. You never judged on things people couldn’t control. Why waste the energy? It really was simply a trust issue. You were at a stalemate. You wanted to trust Sam, you really did. Bobby alone trusting him should've been enough to convince you to, but the General was just too far drilled into your psyche. You had to form your own opinions about a person, regardless of other’s influences, especially if there was a red flag as big as this. It was simultaneously your best and worst quality. Sam had given you no reason not to trust him; then again, you hadn’t really been in a situation to prove that. Bobby had the three of you home all week to test his different theories on how the colt worked. It was a tedious process that required zero violence (unless you count the numerous books thrown at Dean for inappropriate comments…by both you and Bobby). Overall, you decided on being cautiously optimistic. You’d trust Sam for now, but only enough to where you could still pull yourself out if need be.

Man, this gun thing was some serious mojo. None of Bobby’s methods had worked thus far. You were still wearing your light wash bootleg jeans and beat-up black Rolling Stones T-shirt (that you honestly weren’t even sure was yours) from the night before. Bobby sat at his desk analyzing a blueprint of the colt while dismembering the actual one. Dean was busy melting bullets and Sam was doing some research in the other room. Every base was essentially covered. You finished the book about special bullets for colts and set it on the stack with the other essentially useless material. Time for a break. You stood up and made your way to the kitchen, grabbing three cold beers out of the second shelf of the fridge. Walking back into the study, you dropped one on each Dean and Bobby’s perspective desks. “Thanks Y/N/N.” Walking back to the couch, you lifted your bottle in response before taking a swig.

“Hey.” Sam entered the kitchen. Dean looked up. “Hey, what’s up?” It was your turn to look up, waiting to hear the information that Sam had gathered. “Might have found some omens in Ohio. Dry lightning. Barometric-pressure drop.”

“Well that’s thrilling.” Dean had a point. Not the most interesting symptoms of a case. “Plus, some guy blows his head off in church and another goes postal in a Hobby-Shop before the cops take him out. Might be demonic omens” Sam walked into the study to join you all. He really needed to figure out that the hook goes at the beginning. Some dude capping himself in a church would’ve caught your interest immediately. Apparently not Dean’s though. “Or it could be just a suicide and a psycho scrap booker.”

“Yea, but it’s our best lead since Lincoln.”

“Where in Ohio?”

“Elizabethville. It’s a half-dead factory town in the rust belt.”

“There’s got to be a demon or two in South Beach. I mean don’t you wanna see Y/N in a bikini too?” That was your cue to take the (extremely thick) copy of the bullet book you just analyzed and chuck it at Dean’s head. Dammit, the bastard ducked. “Hey!”

“You earned that one and you know it.”

“Ah--fair.” You rolled your eyes and sprouted a half smile.

“Sorry Hef. Maybe next time. How’s it going for the rest of you?” You looked to Bobby, as you had found nothing. He didn’t even look up. “Slow.” Dean looked reminiscently at the gun. “Ah, I tell you, it’s a little sad seeing the colt like that.”

“Well, the only thing it’s good for now is figuring out what makes it tick.” You walked up to his desk and looked over the weapon. “So what does make it tick?” Bobby slowly looked up at you and you immediately raised your arms in a ‘don’t shoot’ position. Sam chuckled and you shot him a look…which he threw right back at you. You were surprised the nerdy one could step up to bat. Dean coughed, breaking the eye contact you and Sam had established. “So, if we want to go check out these omens in Ohio, you think you can have that thing ready by this afternoon?” He had stood up to face you and Bobby at this point. Sam again chuckled; knowing all too well the look Dean was about to receive. And let me tell you, Bobby delivered. “Well, it won’t kill demons by then, but I can promise you it’ll kill _you_.” Dean joined in the small laugh you all shared. “All right. Come on, we’re wasting the daylight.” The boys began walking out. “See you, Bobby.” You threw a hand up and gave them the two-finger salute. You walked to the bookshelf to grab the next assignment when Dean stopped and turned around. “Coming Y/N/N?” You turned your head and stared. “Was I invited?”

“Purely for your own safety. I don’t wanna read tomorrow’s headline ‘Old Drunk Shoots Hot Brunette’.” It was Bobby’s turn to throw the nearest book, this time smacking Dean right in the shoulder. You cracked a smile again. “I’ll grab my bag.” You picked up your black duffel and leather jacket from the kitchen chair. “Hey! You all run into anything—anything—you call me.” All three of you nodded and turned, you throwing one last wink to Bobby, who in response gave you his warning eyes. Right. Case #3 with the Winchesters. Here’s to hoping it goes better than the last two.


	2. The Initial Sweep

**Notes for the Chapter:**

> Don't forget to comment your reactions/suggestions! I try to respond to everybody and if you really have a good idea I will most likely incorporate it somewhere! Thanks again lovelies <3

It’s official. The third time something happens, it creates a habit. You had again been out-voted and forced to take the Impala and leave your Jeep. Not that it really took much coercing, as you didn’t seem to have the attachment to your car that Dean had with his. It was simply for practicality reasons. But hey, no skin off your back. You were woman enough to admit that you admired a classic car when you saw one. You shut the door to the back seat behind Sam and the three of you were off to Ohio.

“There’s not much left for the insurance company. It _was_ a suicide. I saw it myself.” The priest who had witnessed the occurrence was walking the three of you through his church. The ruse this time was that Sam and Dean were insurance brokers and you were a trainee learning the craft. Dean spoke up. “Well, this shouldn’t take long, then.” The priest came to a halt and the three of you followed suit, tracing his gaze to the facing balcony. The priest sighed, sadness in his eyes as he remembered the event. “That’s where Andy did it. It’s the first time I’d seen him in weeks. He used to come every Sunday.” That piqued Sam’s interest. You began to ascend the stairs; having a bit of trouble with the stiff black pantsuit you had picked up on the way. The problem with your body type was that while one size fit your waist, it certainly did not fit your ass and vise versa. You (unfortunately) had to accommodate your waist this time, making your ass look extremely prominent. It just felt wrong in a church. Apparently Dean noticed as well, as (unbeknownst to you) Sam had to elbow him to direct his attention back to his notepad. He grimaced and snuck one final look before going back to his task. You finally reached the top to analyze the crime scene when Sam spoke. “When did he stop?”

“Probably about two months ago. Right around the time everything else started to change.” Dean took notes as you searched the area for sulfur. Sam continued his questioning. “Change how?”

“Let’s just say this used to be a town you could be proud of. People…cared about each other. Andy sang in the choir and then one day, he just wasn’t Andy anymore. It was like he was…”

“Possessed?” Sam finished his thought. “You could say that. Gambled away his money, cheated on his wife, destroyed his business. Yes. Like a switch had flipped.”

“Father, did you know the man who killed those folks in the Hobby-Shop?” You looked up from your position on all fours to hear his answer. “Sure, Tony Perkins. Good man.”

“Would you say that is personality suddenly changed one day, too?” You studied the priest as he thought. His eyes twitched to the right, an indication that a connection was made in his mind. “I never thought about it that way, but…yes. About the same time as Andy, about two months ago.” You looked to Dean and nodded, indicating that the priest was being honest. He looked to the man, “Well, thank you, Father. Appreciate your time.”

Sam looked up at you as you descended the stairs joining the brothers once more. “Well, I thoroughly checked and there was no sulfur.”

“Well, did you hear that? Two months ago, we opened up the Devil’s Gate. What, all of a sudden this town turns into Margaritaville? It’s no coincidence.” You sighed, knowing full well that you were missing something. All signs pointed to demon, so why was there no sulfur? No one had contaminated the crime scene. It was time to find a room and reassess.


	3. Richie

Dean unlocked the door as the three of you entered the motel. You counted two beds when Dean chuckled. You looked to see the cause, which lead your gaze to the ceiling. Jesus Christ, there was a ceiling mirror. “I’ll take the couch,” you announced, knowing full well that it’s probably the most sanitary out of the sleeping arrangements, though not by much. Sam threw his stuff on one bed and Dean mirrored him on the other. He was still chuckling to himself about the ceiling mirror as he walked over to close the door. You began unpacking your duffel, setting out your gun and taking the knife out of the right side pocket. “Richie?” You turned around to see whom Dean had addressed. “I don’t believe it.”

“Hey. Dean…Winchester, right?” The man Dean had noticed was a short, greasy fellow wearing a wife beater under a brown and yellow sweat suit, a gold chain, and a fedora. God, this dude screamed sleazy. “Yeah.” As Dean answered, a woman, who was clearly a prostitute, walked out of the same room. You sat down on the couch and crossed your legs, interested in knowing just how exactly the older Winchester knew this goon. “Oh, uh…this is my sister, uh, Cheryl.” Dean eyed the woman, clearly unconvinced. “Hi Cheryl.” Richie counted some money and gave it to the woman. “There.” All three men leaned outside of their doors to watch ‘Cheryl’ walk away. You rolled your eyes. “Well, you know…stepsister.”

“Come on in. This is my brother, Sam, and our friend, Y/N.” Richie zoned in on you and you instantly knew his next move. He walked over to you, a smirk on his face. “Well, hello beautiful.” He extended his hand and you reached yours out simply to be polite. He grabbed your hand and kissed it, making you, and probably everyone else in the room, a bit uncomfortable. Sam coughed, saving you for the moment and redirecting Richie’s attention. “Hey. How you doing?”

“Not too bad. How do you two know each other?” Ah, the question of the hour. Richie, much to your chagrin, decided that this was the moment to take a seat uncomfortably close to you on the couch and gestured to Dean, urging him to tell the story. Dean looked to Sam. “Well, you were in school…” Richie nudged your arm with his elbow, “It was that succubus, right?”

“Yeah, yeah”

“Oh, man.” Clearly there was a story behind this that you honestly weren’t sure you wanted to hear. “You shoulda seen the rack on this broad.” Sam instantly coughed again and looked down. He then peered at you from under his bangs; probably embarrassed that Richie made such a vulgar comment in front of a stranger. It was actually kinda cute.

“Freakin’ tragedy when I had to gank her.”

“Whoa, whoa. Wait. Who killed her? If I remember, your ass was toast until I showed up.” Right. You couldn’t exactly see Richie being competent at much in the hunting universe. Then again, it could just be your bitchy side talking. This dude really was rubbing you the wrong way. Literally. His hand would brush your leg on ‘accident’ as he told his story. You were two seconds away from breaking his wrist. “Oh, I forgot what a comedian this guy was.” Richie’s cellphone had begun to ring. “Richie, Richie. I told you then. I’ll tell you again. You’re not cut out for this job. You’re gonna get yourself killed.” He gave Dean a look and stood up (finally). “Talk to me…FYI Winchester, words hurt…yeah? No, it’s not a good time, baby. Later.” He hung up and winked at you as he returned to his seat. Gross. You looked to Dean for help. He simply smirked, enjoying how uncomfortable you were. “So you find anything in this town anyway?”

“Uh, no. I got nothing. Oh, wait a minute. You mean as in demons and whatnot?”

“Yeah.”

“No, I got nothing.”

“Typical. What about your sister back there?”

“Honestly, she definitely had the devil in her, but she wasn’t no demon, you know what I’m saying?” At this point he had his entire hand on your upper thigh and gave it a small squeeze. You jumped up quickly. “Sam! I need something in your bag.” Sam looked confused for a brief moment, but once it clicked, he tried hard to stifle his laughter. Richie continued. “Right. Seriously. Church guy, Hobby-Shop guy…they were lunchmeat by the time I got there. Maybe they were possessed, but I can’t prove it.” You dug around in Sam’s duffel until you found a giant bottle of conditioner. Pulling it out, you looked at him questioningly. He grabbed it out of your hand, embarrassed. You smirked at him as he averted your eyes and turned to Richie, “Yeah, that’s where we are, too. Let’s just say the demons are possessing people in this town. You know, raising hell…”

“But why would a demon blow his brains out?” you intervened. Richie answered (of course). “For fun? He wrecks one body, moves to another. Like taking a stolen car for a joyride.” Dean got an idea. “Anybody else that fits the profile? You know, nice guy turned douche that’s still breathing?”   
“There’s Trotter.” You zipped up Sam’s bag, finished with your ruse. “Who’s that?”

“He used to be head of the rotary club. Then people say he turned bastard all of a sudden. Brought in the gambling, the hookers. He practically owns this whole town.” Sam stepped back in. “You know where we could find him?”

“Oh, he’ll be at his bar in a few hours.” You heard vibrations and looked over to see that Dean had turned on the magic fingers. You ran your fingers through your hair, a bit overwhelmed. This was the first time you were actually bunking with the boys and you were used to having solitary spaces and silence during hunts. After Richie’s advances and the unpleasant picture of Dean using the magic fingers, you really needed some ‘you time’. “Going for a walk. I’ll hit you guys at the bar later.” Before you even left the room, Richie looked to Dean. “Hey, you hittin’ that man?” You turned around outside of the doorframe to see a sleazy grin on Dean’s face, but it was Sam who spoke up as you made your way back down the hall. “No, he’s not. But he wishes.” What you would’ve given to see the bitch face Dean made after that comment…


	4. The Bar

**Notes for the Chapter:**

> Don't forget to leave Kudos and comment! :)

You checked your watch and realized you had less time to clear your head than you thought. The address that Sam had texted you was about a half hours walk and you were supposed to meet there in forty-five minutes. That gave you fifteen minutes to collect your thoughts and wipe off whatever disease Richie had most likely carried. You decided to take out your phone and text Bobby an update. _‘So far so good. Nothing concrete yet, but something is definitely going on in this town’._ Tucking it in your back right pocket, you inhaled the fresh air and closed your eyes. Opening them, you instantly spotted what you had to do next. If you were meeting this guy at a bar, you were going to need the perfect dress.  
  
You entered the store and walked straight up to the dress that caught your eye. It was a black-haltered mini with a bit of lace on the top. You had still yet to buy a new hustling dress since yours had turned to ash the first time you worked with the Winchesters. Guess now was the time. Though you were gonna need shoes to complete the look. For hunting purposes, of course. You wandered into the heel section and picked out a pair of simple black stilettos with a strip of fabric running down the middle. Perfect, one more thing checked off of your ‘to do at some point’ list. You paid and checked the time, realizing you were gonna get there a bit late. Eh, oh well. You honestly doubted that the men would mind.  
  
You entered the bar and raised your eyebrows. Wasn’t this supposed to be some boarded up factory town? Everywhere you looked there were either sleazy men not even trying to hide the fact that they were staring at you or skanky women giving you death glares for distracting the customers. Either way, you were uncomfortable. You spotted two familiar looking backs facing a familiar greasy face wearing a pink satin shirt. You strutted towards the men; glaring at a few questionable characters that ‘accidently’ brushed (or straight up grabbed) your ass. You were close enough to catch the end of Richie’s gimmick when he spotted you. “Ah, forget about it… Is that you beautiful? You sure cleanup well. Excuse me while I pick my jaw up off the floor.” Both Sam and Dean turned to see the woman Richie had just put the moves on. Their reactions (while completely opposite) meant essentially the same thing. Dean stared, starting from your shoes all the way to your face, both an eyebrow and a corner of his mouth raised. Sam swallowed and became uncomfortable looking around for any kind of distraction, panicking a bit when he only saw more scandalously dressed women.  
  
“Sorry boys, had to pick up a few things. I miss anything good?” Dean bit his lip. “Not a thing. But hey, that dress looks great on you…and just for the record, so would I.” He wiggled his eyebrows as you simply raised yours in disbelief. “What?”  
  
“I’m debating whether to hurt you physically or emotionally.”  
  
“Kinky.”  
  
“Shut up. So where’s this Trotter guy?” Richie answered with eye contact that wasn’t exactly as high as it should've been. “He’s over there. He sits there all night. Can’t touch him.” You looked to where Richie gestured. There was a bald man dressed in all black, apparently discussing business with another man. Sam cleared his throat, finally getting a word in. “So, what do we do now?” He still refused to look directly at you but Dean’s attention was already shifted to another woman. “I don’t know about you guys, but I’m gonna do a little investigating with that bartender.” Richie apparently was having none of it though. “Easy. Me and her, we got a little somethin’-somethin’ lined up for later.”  
  
“Yeah, right.” _Your thoughts exactly._ The only woman you could picture with Richie was one that he paid. “Stings, don’t it? By the way, if you’re interested beautiful, you are certainly invited to that as well.”  
  
“I’m gonna have to pass.”  
  
“Not a group kinda lady, I can respect that. All right. I gotta hit the head. Release the hostages. Be back in a few.” Richie turned and walked away. You made a fake gagging noise and Sam chuckled a bit. Finally some acknowledgment! You smiled and looked up, catching the eye of a rather handsome stranger. This guy had perfect teeth and a crooked smile; a rare combination. His green eyes paired nicely with some neatly styled brown hair. By the looks of his outfit, this man was just getting off of work and you didn’t see any evidence of a wedding ring. You established eye contact and he responded well. “Well, on that note, I’m gonna do some research of my own.” You flipped your hair and took the first step towards your target when Dean lightly grabbed your arm getting your attention. You turned and leaned toward him to hear what he had to say. “Hey, maybe you should just take it easy and stick with Sammy tonight. Pretty sure Bobby would kill me if he found out I let you do _that._ ” He gestured to the stranger. You smirked and brought your hand up to cup Dean’s cheek, your thumb running over his stubble as you smiled sweetly. “You’re cute.” You slapped it twice and again made your way to the mystery man, the older Winchester dumbfounded as to what had just occurred.  
  
Time to make your move. “Now is it just me, or do you seem to be the only respectable looking man in here?” The stranger responded, his voice a smooth mixture of chocolate for your ears. “Well I’m not exactly sure, your friends over there look pretty decent to me.” You looked at Sam and Dean to find that Dean’s attention had redirected back to the bartender and Sam was staring at you. That is until your eyes met his and he quickly looked elsewhere. You furrowed your brow, still trying to fully understand the younger Winchester. “What, them? Friends of my father’s. More the protective type than the romantic ya know?” He smiled, showcasing his teeth once more. God, you had a thing for nice teeth. “More than you know actually. My name’s Noah.” He extended his hand and you shook it. “Y/N. Nice to meet you.” You smiled back at him and noticed that just over his shoulder, you still had a visual on Trotter. You weren’t completely blowing off your responsibilities. He was still only talking to a few men, glancing at women every now and then. He may be a bit pervy, but nothing yet indicated that he was demonic. You shifted your attention back to Noah. He apparently worked the office portion of the local bank. Not a bad career.  
  
The two of you talked for a while more, inching closer by the minute. He was in the middle of an amusing work story and playing with your hand when you saw a blur of Dean run past you. Cue gunshot. A high pitch scream sounded (that wasn’t you by the way) and you found yourself shoved towards the shooter by Noah, whom had practically left skid marks on his way out of the building. You had never been more turned off. You turned back around to see that Dean had tackled the shooter and Sam was already splashing him with holy water. You made your way there, placing your hand on Sam’s back to indicate your arrival. The holy water had no effect other than to utterly confuse the man. “Hey, what are you doing?! He slept with my wife. That bastard slept with my wife!” The three of you shared a look. This man was not possessed in any way. You looked to the people left in the bar, most of them simply staring. You took the opportunity to be proactive and diffuse the scene. “Somebody call 911!” The bartender followed your orders and your gaze shifted over to Trotter…who was already staring at you…

**Notes for the Chapter:**

> Also for those wondering, this is the visual for the dress and the shoes. It should be the very first result on each link. :)
> 
> Dress: https://www.pinterest.com/pin/319896379773576606/  
> Shoes: https://www.pinterest.com/pin/319896379773576647/


	5. Sleepover

You sat in between the brothers, having just been questioned by the police. The tension rolling off of Sam was palpable. “Too many cops here. I say we roll.” You’d agree, but that would look too suspicious. Trust me, you knew your way around law enforcement. Dean apparently did as well. “Just be cool. Poor jerk. Only thing possessing him was a sixer of Pabst.” You stared as the officers escorted him out of the building, waiting for the right moment to speak up. “So, what’s the deal, then? People in this town getting possessed or not?”

“I don’t know. Maybe it is just what it is; town full of scumbags.”

“You can say that again. Dude I was with could’ve medalled in the Olympics with how fast he ran outta here when the gun went off, not to mention he shoved me _closer_ to the shooter. Coward.” Hunting almost ruins you in that sense. Men willing to take a bullet for you just becomes as polite as opening doors, making the normal ones that wouldn’t much less appealing. An officer walked up to the three of you, interrupting your discussion. “You three ready for your mug shots?” You all froze. “The photographer’s gonna be here in a few and take your picture for the local paper.” Simultaneously, you all exhaled. Dean charmed it up, apparently a specialty of his. “Be an honor, officer. What a thrill! Haha.” Sam stood. “Yep. Time to go.”

“Agreed.”

“Wait a second. Wait a second.”

“What?”

“Where’s Richie?” _Dammit…_

You’d decided at the bar that you all would wait a night and if he still hadn’t shown up by the next day, you’d make a plan. Regardless, the three of you needed to bail before your mug shots were displayed all over town. You made your way down the street, only getting cat called a grand total of three times before reaching the impala. Sam opened your door for you before moving on to his own. “Thanks, I almost forgot that chivalry was a thing.” He smiled, actually making eye contact for the first time since your new threads. “I can see why. I feel like even _I_ need a shower after that second comment.” You laughed and slid into the leather seat, Sam closing the door behind you before entering the car himself.

The ride back to the motel was uneventful. You stepped in the room and made a B-line for your duffel. “I call first shower.”

“Whoa, whoa, whoa. I don’t know how you do things, but around here, eldest gets the privileges of hot water.”

“Says who?”

“Me. You wanna roll with us, you gotta follow our rules.”

“Fair. But what if I make you a deal?”

“I think I’ve had my fair share of deals recently.”

“It’ll be worth your while.”

“Nope. Non-negotiable.”

“C’mon just humor me!”

“Fine! What’s on the table?” You thought for a moment. Gaining an idea you looked Dean straight in the eyes. “Strip tease. All yours if you enact a ‘ladies first’ policy.”

“Bull. You’re full of it.”

“Am I?”

“Not gonna work. I know you’re screwing with me.”

“But what if I’m not? You're really willing to miss the opportunity?” It was Dean’s turn to contemplate. “Dammit, I’m so getting boned for this. You drive a hard bargain. Well played Weston, you officially get first shower.” You smiled to yourself, a small victory having just been won. What? You were really desperate for a shower after the day you’d had. You grabbed your night supplies and headed to the only bathroom. “Hey, aren’t you forgetting something?”

“Right!” You placed your things on the nearest bed and faced Dean. Sam showed symptoms of upcoming panic, clearly not wanting to be a part of this. _He doesn’t even know what’s coming._ Slowly, you unsnapped the clasps of your bra over your dress and slid your arms out of the straps, one at a time until you pulled the entire contraption out of the side. You watched Dean's eyes scan your body and then flit from side to side in anticipation. You unzipped the back of your dress, making sure that he was taking inventory of every inch you were exposing...and then flung the bra at him. You made your way back to the bathroom laughing. “Congrats Winchester. You earned that.” He caught the lacey black bra and simply stared at it. He looked up. “Hey, we had a deal!”

“We did. I stripped and you’ve officially been teased. Nice doing business with you.” Dean stood dumbfounded as the bathroom door closed. He looked to Sam, who found the entire ordeal quite amusing and was outright laughing. “I’m slightly hurt, but mostly turned on.” Sam’s laugh turned into a grimace.

It felt amazing to get the sleaze of about a dozen men scrubbed off of you. Your entire mood had shifted as you slid your sweatpants on. You felt grounded, at ease. There was just no satisfaction like getting clean after a long day. You took your hair out of the towel and hung it back up, allowing stray droplets of water to fall from your long dark locks. You opened the door to defog the mirror. “Shower’s yours.” You called. You grabbed your toothbrush and toothpaste from your pile and began brushing. Dean entered the bathroom and you noticed his aura had changed as well. With no distraction, he had most likely spent the entire forty-five minutes of your shower doting on Richie. You almost felt bad. You leaned in to spit toothpaste into the sink and rinse your mouth. Dean turned the shower on and you cut a string of floss. Dental hygiene was something that tended to slip through the cracks with hunters, and you were certainly not okay with that. You were on your last row of molars when Dean turned away from you and slipped his shirt off from behind his neck. Objectively speaking, he really was well sculpted from the back. You took a moment to admire it and then finished your teeth, discarding the floss. “Night.” Dean nodded in response and you closed the door behind you.

The room was empty, Sam probably having gone out for ice or something. However, he walked in a moment later yes, carrying the ice bucket in one hand, but also a stack of several blankets and a pillow in the other. He set the bucket on the table and turned to the couch. “I didn’t know how cold you get at night. I could get another blanket if you need it?” Warmth spread through your chest. “Two’s perfect. Thanks.” You smiled at him as he set the stack down and went to grab his shower supplies to have ready. Usually running hot, you placed one of the blankets down to cover the (probably contaminated) sofa and laid on top of it, spreading the other one over your body. You reached over and grabbed the knife that you had unpacked earlier, tucking it perfectly under your pillow. Dean walked out of the bathroom, still heavy in thought. You turned your back on the men and shut your eyes. “Night guys.”

“Night.” They said in unison. Both brothers stared for a moment at the body of the platonic female hunter sleeping on the couch during a hunt. It was a first for everyone.


	6. Our Bad...

“Well the offer still stands, baby.” Gross. There wasn’t enough showering in the world that could get the sleaze off of you until you officially left this godforsaken town. You never thought you would get annoyed with men making advances. Every woman knows there’s a slight ego boost every time it happens, but this was just excess. However, this one was only the latest, the bartender. “The answer is still no buddy. Thanks for the beers.” You slapped cash on the counter and grabbed the three beverages, taking them to the table Sam and Dean currently occupied. You weren’t even trying today. Light wash jeans and a purple flannel didn’t exactly scream _come get me baby._

Dean was glued to his phone and Sam simply stared at him. You set the beverages in front of them. There was still no sign of Richie and Dean was fixating. Sam spoke up. “You realize there is red meat within striking distance right?”

“How many times do I have to tell Richie he’s gonna get himself in trouble?”

“Dean, you’re assuming he’s missing. I mean, maybe he just bailed.” Sam had a point. It didn’t seem unlike him. Actually, it fit the profile well. “Look, he’s a moron. He’s a sweet moron, but he’s not a coward. He wouldn’t just bail. I got to go find him.” You weren’t actually implying Richie was a coward, hell, his assertiveness in his advances contradicted that completely, but you could see him simply losing interest, or rather gaining interest in another area. Sam sighed, knowing he wasn’t going to get Dean to back down. “All right. Meanwhile, I think I’m gonna trail this Trotter guy.” You turned to Sam. “Mind if I join? There was something about the way he looked at me last night that I just didn’t like.” Dean snorted. “Y/N/N, you’re a hot chick in a skeevy town, I doubt you’ll like half the looks you get.”

“No, this was different.”

“Whatever you say.” Dean stood and made his way out of the bar. You watched him leave, his beer untouched. Speaking of, you grabbed yours and took a sizable swig. This town didn’t need to be taken with a grain of salt, it needed the shot of tequila. Seriously. At the current moment, six guys (including the bartender) were giving you sex eyes. And after the whole Noah fiasco, you weren’t itching to respond to any of them. You turned to Sam to see if he was having similar issues, but his focus was elsewhere. You followed his gaze to see Trotter leaving out the back. Sam stood suddenly. You understood immediately. “I got your six,” you stated as you packed your gold-plated desert eagle in the back of your jeans.

Trotter lead you and Sam to what looked like it used to be an official town center. Sam entered first and you slid your gun out of your jeans, cautiously scanning the perimeter. This was your element. He led you to the hallway, an adjoining one splitting it right at the center. Peering out, Sam concluded that visual was too risky and immediately jolted back, you following suit. He gained just enough room to investigate when his phone went off. _Damnit Sam!_ He answered before anyone noticed. “Dean. Yea. Hey. I can’t talk right now. Yeah, I’m fine. Just meet me at the bar in twenty minutes, okay?” He hung up as the two of you heard footsteps walking in your direction. You retreated to the previous bend, hiding yourselves from the goon’s sight. You held there for another minute as Trotter completed his business and left. Still on the offensive, you and Sam entered his office, your gun ready. You began snooping through his files and desk trinkets. There weren’t many decorative items other than a vintage lamp and pencil holder. You were under the desk searching for hidden compartments when you heard a grunt. You shot up to see Sam kicking the crap out of a rather large man. You saw Trotter approach with a gun raised. Pressing it to Sam’s head, you realized that he hadn’t noticed you yet. You quickly ducked back down. “What are you doing here?”

“I think maybe you know.” You were trying to find a route to ambush Trotter, but the angle that his men were at made it very easy for them to spot you immediately should you try. “Yeah? Well, I think I’m calling the cops.”

“Cops?”

“Breaking and entering, assault. You’re in a peck of trouble, my friend.” Getting one over on Trotter suddenly seemed a lot less imperative. You sat down, your back against the desk. Sam was floundering. “Uh, well, I think I could probably explain it!” He swiftly twisted and grabbed the gun from Trotter. “All right, back up! Get Back.” Trotter panicked. He retreated a few steps and held his hands up. “Money’s in the safe! Take it and go.”

“I don’t want your money. I just gotta be sure.” He slowly took out his holy water flask. Well, this wasn’t going to go well. Although, you probably would’ve done the same thing. Better to be 100% sure. He flicked the water onto Trotter, who did nothing but make a surprised sound. He then hit the goon, who had much of the same reaction. Trotter was plain irritated now. “What kind of psycho are you?” Sam quickly found his answer and understood the awkward situation he had now gotten himself into. “Oh, god. Uh, I’m sorry heh. I think this was just a minor misunderstanding? Yeah, okay, um. How ‘bout I just leave, ‘cause…you know, I’ll take these (he emptied the chamber of the pistol). I’ll, uh, I’ll leave this (referring to the pistol) for, uh…you, uh…have a nice day?” He smiled and awkwardly set the gun on the table before high tailing it out of there. Smooth Sammy. Crap. Might as well bite the bullet. You popped up, surprising both men. “Uh…sorry.” You speed walked out of there to meet Sam outside and hopefully forget that ever happened.


	7. 40 Bucks

If you didn’t need alcohol before, you certainly needed it after that whole ordeal. Lucky for you, you and Sam were supposed to meet Dean at the bar. Sam was on edge; not even registering the female attention the prostitute across the bar was giving him. You didn’t blame him either. Dean was fifteen minutes late. Not quite enough to full on panic, but enough for the both of you to constantly check the time. The hooker certainly noticed, finally making her move on Sam. “You look kind of tense. You know, I know a surefire way to relax.” Sam, however, was clearly not interested. “Maybe later.” Wow. A bit sassy for the younger Winchester, who had apparently reached his waiting limit for Dean. Sam redirected to the bartender. “Excuse me. Hi.”

“What can I get for ya?”

“Um, you remember the guy I was with last night? We sat right here. Um…”

“The big hero who jumped on Reggie.” You couldn’t have rolled your eyes any harder. “Yeah, yeah. The—the big hero. Right. Um, have you seen him around at all today?”

“Maybe. Depends.”

“D-Depends on what?” Oh Sam. Sweet naïve Sam. The bartender simply smirked. “Oh, my—Does everyone around here have their hand out?” Sam was really getting irritated. Whenever it came to big brother, the big guns came out. Sam frantically checked his jacket, unable to find anything larger than a 5$ bill. The bartender raised an eyebrow. Sam hesitated, then looked to you with these puppy dog eyes that he was apparently famous for. You sighed and glared at the bartender, pulling a twenty out of your back pocket. It was your turn to step in. You slapped the cash on the counter, making the bartender smile. “He left with Casey about an hour ago.”

“Any idea where they went?”

“Her place…for bible study.”

“You got an address?”

“What’s wrong with you? You think I’m gonna give you a co-worker’s address just so you two can go over there and get your kinky rocks off with each other?” Dammit, you were going to have to pull out your emergency 20. You rolled your eyes and slipped it out of your bra, practically shoving it at the bartender. “Corner of Piermont and Clinton. You two have fun.” He walked away and you glared at Sam. “Dean owes me forty bucks.”

The two of you left the bar, ready to rip Dean a new one for ditching you guys for some ass, not to mention costing you forty bucks in the process. You arrived and Sam knocked on the door, which creaked open without much persuasion. “Dean?” You both were on edge, praying to god that you weren’t gonna witness something that you couldn’t come back from. Sam stepped on a pair of piggy slippers. Gross. Certainly not your kind of style. Come to think of it, based on your initial analysis of Casey, they didn’t really fit hers either. As a matter of fact, nothing in this place seemed to fit her profile. A photo with a man that seemed long term with a cross placed over it was the most suspicious of all. This really rubbed you the wrong way. You walked over to investigate the item when your attention immediately shifted. You flipped the picture on its face and ran your finger along a yellow substance behind it that you pretty much already knew what it was. You brought it to your nose and sniffed. “Sulfur.”

Sam led the way as the two of you trudged back into the bar. You faintly heard _Thunderstruck_ and realized your phone was going off. Bobby. It’s about time, you texted him yesterday. You held a finger up to Sam and ventured into the quietest corner while he went to, yet again, berate the bartender. “Bobby?”

“Yea it’s me. Listen I have an update…”

“I’m actually gonna interrupt you ‘cause we’re kind of in a situation. See, we found some sulfur and Dean’s missing. Turns out there _are_ demons in this town and they seem to have found one of us as well.”

“Well that’s certainly a different tune than your text sang yesterday. I’m on my way. By the way, colt works. You’re welcome. You and Sam try to find Dean and—“

“What is it with the people in this town?!”

You heard that from across the bar. Time to step in. “Yea Bobby thanks, see you soon.” You hung up without even hearing the rest of what he had to say. Quickly, you joined Sam at the bar. “Okay, hey let’s get out of here and keep looking. Bobby’s on his way and—“ Sam’s attention shifted and he began walking in a specific direction, cutting you off. You looked at his target to see the father sitting alone at a booth. Guess he found his next lead. “Father?”

“Yes?”

“Um…Can I talk to you for a sec?” The father nods and gestures for the both of you to slide in, Sam first. “So, the—the bartender the other night, Casey, you know her pretty well?”

“Since she was in pigtails.”

“Well, um, she and my brother, they, uh…” _Don’t say it Sam. We just left an awkward situation!_ “They…left tonight. Together.” Guess your telepathic skills were a bit rusty.

“Ah. Well, not that I approve, but they are consenting adults.”

“Right.”

“I’m sorry. You said ‘Brother’? I thought the two of you were insurance investigators?” Honestly, it hadn’t even occurred to you to keep up the ruse after everything that’d happened since then. “Right, right. Well, we are. Um, it’s like a family business, you know?” The Father furrowed his brow and glanced at you, clearly wondering how you fit into the picture. Sam followed his gaze and realized he had to think quickly. “She’s my wife.” Married. Got it. You placed your left hand on Sam’s bicep and smiled. The Father then glanced at your hand before looking to you with his eyebrows raised. Your turn. “Getting the rings engraved. December 18th, the day we met.” You finished it with a kiss on his cheek. Specific dates and physical affection that wasn’t too over-the-top kept the questioning down to a minimum. Though the Father seemed satisfied, Sam was just downright uncomfortable. “Anyways, um, so, I went to Casey’s apartment and they weren’t there. Um, I just have this feeling that they—that they might be in trouble.” That caught both yours and the Father’s attention. You couldn’t tell if Sam was putting on a show for him or he actually thought Casey was a victim as well. Regardless, your profile wasn’t wrong. The Casey that you initially examined at the bar was in no way even related to the one you found at her apartment. The Father’s attention was grabbed for a different reason. “What kind of trouble?”

“Just trouble. Please, father, I need your help. Is there anything you could tell me about Casey—anyplace she’d go, maybe?”

“Yes, there is a place. Let me get my jacket.”

“No, wait, father. I don’t wanna put you out, we can do this ourselves. Right honey?” You looked to the Father and nodded with a smile. “Listen, if Casey’s really in trouble, then there’s nothing to talk about.” You didn’t know why, but the hairs on the back of your neck stood up with the eye contact that the Father made with you. You narrowed your eyes. If you’d learned one thing since coming back from California, it was to trust these feelings. You had your eye on him…


	8. Instincts

You rode in the back of the Father’s car, your eye on him the entire time. Sam was oblivious, which you half expected. Based on the history of the Winchesters that you’d been told, whenever one of the brothers was in possible danger, the other lost all sense. It was part of the reason you felt they needed a third member. On top of your skills (that both men sorely lacked), they needed a voice of reason; someone to talk them off the ledge and keep them sane. While Bobby was great at fulfilling that role, he had responsibilities of his own in Sioux Falls. Sure, third-wheeling wasn’t your first choice, but hunting with the Winchesters was beginning to grow on you.

“So, insurance investigating. You enjoy the work?” The Father glanced between you and Sam, the one in the front seat answering, “Yeah. Yeah, I…like being able to help people.”

“Ever think about doing anything else?” That response cut off Sam’s answer. The Father was getting antsy. The issue was figuring out if he was just worried about Casey or if he was driving you and Sam to your doom. Regardless, you didn’t trust him. “Like what?”

“Mmm, anything. You seem like a pretty smart kid. Somehow I see you out in front of the pack. You could do some great things.” Why the sudden buttering up of Sam? This dude was getting worse by the minute. “I don’t know. I like doing what I’m doing, I guess.”

“Well, it’s your life. Does, um…Dean?”

“Yeah, Dean.”

“Does he find trouble often?” More than you know sir. Or maybe you already know. The hairs on your neck were still on edge, much like the rest of your body. “Yeah. Yeah, Dean finds his fair share.”

“Well, it’s a good thing he has you—His brother’s keeper.” Sam awkwardly smiled. If you weren’t getting evil vibes from this guy, you’d say they might have been bordering on gay.

The three of you pulled into a driveway moments later. The Father cut the engine and turned out the headlights. You reached around and felt your gun still in place, just in case. You tried your door and were slightly surprised when it wasn’t locked. Stepping outside, you immediately clocked the impala. Sam did too apparently. “Dean?!” He pounded his fist on the front door yelling his brother’s name yet again. No one answered. He was in brother mode again, thinking nothing of rationality or strategy until Dean was in viewpoint. It was like seeing a child panic until they had a sight of a parent, and frankly, it was downright uncomfortable. Sam indicated to his left. “You two check that way.” Perfect. Some alone time with the suspect was just what you needed to figure him out.

You followed behind him, watching the black coat sway in the slight breeze. He didn’t seem worried to you anymore, an indication that it was option B…he had something planned for the two of you. You glanced at his reflection in the mirror of the windows. He was smiling. Not only that, but after shifting your gaze about three inches up what do you see other than black eyes. You immediately reached for your gun and shot two bullets into his back. “God, I hate when I’m right.” He slowly turned towards you, unphased. “Figured it out, huh Weston? So what’s the plan now? You shot me. Good for you, I honestly wasn’t expecting you to catch on so fast. But see, now it’s my turn.” He raised his hand and threw your gun in the direction of the impala, leaving you rubbing your wrist. Dude had a point, there really wasn’t more of a plan. Guess winging it would have to do. You pulled your own holy water flask out and held it at the ready. He took one step in your direction and you sprayed him immediately. “AH!” His eyes went fully black at this point. “I knew I should've left the bitch at the bar.” You threw a second dose and he blocked it with his arm, which began to sizzle. Throwing one last dose, you thought you had him and could start reciting the exorcism. Not the case unfortunately. He grabbed your wrist mid-throw (completely disregarding the dousing his forearm caught, something you hadn’t counted on) and twisted it. You mildly grunted and threw a punch with your other arm, landing right on his nose. He punched back, giving your chin quite a shiner. You went to retaliate when the wrist he had a hold of, he twisted behind your back. Since you were mid-punch, it threw your entire momentum off and he ended up getting both hands locked in his one. You opened your mouth to yell for backup when his free hand covered it. Dammit.

Shoving you in the direction Sam went, you were forced to cooperate. You turned the corner to see Sam, who clearly wasn’t expecting a hostage situation. He floundered, not knowing which mode of action to take. _BANG!_ A nearby statue’s head blew off. Two out of the three of you turned to look in the direction of the shot, seeing the one and only Bobby Singer. You decided that this was a perfect opportunity to free yourself. Without missing a second, you threw your head back, nailing him once again in the nose. He threw his own head back and you tucked and rolled in Sam’s direction. He looked pissed now. Raising one hand, he sent you flying to your right, directly into said statue, forehead first. _Ouch._ He then moved onto Bobby, sending him onto the concrete a few feet from your position. Last came Sam, who already had given him one or two good douses of holy water. He got thrown into the windshield of the Father’s car. Hey, at least it wasn’t you who had to pick glass shards out of her body this time, although, the blood running down your temple wasn’t ideal either. Bobby apparently agreed, as he was by your side in a second. “Y/N/N, you all right?” You did a sort of moan in response. “Never better.” You tried sitting up, your back against the statue. There was a throbbing in your head that really wasn’t pleasant, although, it seemed more indicative of an impeding migraine than any serious injury. Sam met up with the two of you shortly after. “You two good?” Bobby answered, thank god, as speaking at the moment was a bit painful. “Yeah.” He quickly handed the colt to Sam and pushed him off. “Go. We’re fine here.” Sam looked back once more to double check and a blonde woman appeared out of the trees. “You heard the man, go.” He nodded and followed the Father inside, the blonde disappearing shortly after. You turned to Bobby. “Who was hunt-with-me-Barbie over there?”

“Long story for another time.”

“Right, let’s tell it when my head doesn’t feel like a caveman tool.” He smirked. You always knew how to ease a situation when Bobby was tense. Two gunshots interrupted the joke. Assuming demons didn’t really need guns, you figured Sam had gotten there in time. You leaned your head against the statue and closed your eyes. You were finally leaving this godforsaken town.


	9. Debts To Be Paid

**Notes for the Chapter:**

> Alas we have reached the end of the story. Thanks for sticking with it and I'd really appreciate kudos and comments letting me know your thoughts about your character! I am also very open to suggestions as to things/traits you would like to see. Thanks Loves!!

How you had managed to get out of that entire situation with only a minor scratch and a migraine was a mystery to even you. You had finished packing your big duffel, placing the smaller toiletry bag carefully inside. About to pick it up to load into the car, a giant set of shoulders snagged it from you. “Seems like you could use a bit of chivalry.” You looked up and smiled at Sam. “Careful Winchester, I might mistake you for one of the good ones.” He laughed. “Shut up. Go ahead and meet Dean and Bobby by the car, I’m gonna finish packing up and I’ll bring your stuff down with mine.”

“Thanks Sam.”

“No problem.” You smiled at him as you made your way out of the room. It still was extremely strange having not one, but two people looking out for you. Still, it was a good kind of strange. The kind of strange that felt fragile. Then you remembered hell and Dean’s deal, realizing that it was indeed just that. Speaking of the older Winchester, you saw him shut the trunk of the impala, deep in a serious conversation with Bobby. Well, you just couldn’t have that now could you? You walked up to the two. “You, sir, owe me forty bucks.”

“What? For what?”

“See, baby brother inside went all crazy looking for you and I ended up having to fork over forty green ones to the bartender for information. Pay up Winchester.” He smirked and looked to Bobby, clearly awaiting the ‘you don’t owe her a damn thing’ speech. He simply shrugged. “After putting up with the two a’ you for an entire weekend I’d say you owe her more.” Dean raised his eyebrows and dropped his jaw. You simply smirked as he looked back to you. Rolling his eyes, he pulled out his wallet and took out two twenties. You reached for them when he pulled his hand back. “Do I get another strip tease? A real one?”

“Another what?!” Clearly Bobby was not amused. _Low blow Dean._ You snatched the cash and practically ran towards the back seat of the impala. “Nothing! Thanks for the cash, jerk!”

“Tease!” You shut the door right at the moment Bobby smacked Dean upside the head. You’d never get tired of seeing that man get slapped…which scared you remarkably less than it used to.

**Notes for the Chapter:**

> Again thanks guys! Fear not as "Bedtime Stories" has been written and sent off to my editor. I should have the first chapter up within the month. Don't forget to leave kudos/comments. I LOVE THIS FANDOM!! xoxo-JC


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